Sodium Hydroxide → HCID 68385179, compound

HRID 534224Notes

Reaction equation

HRID 534224 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5]([CH2:12][N:13]([C@@H:20]2[CH2:22][C@H:21]2[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)C(=O)C(F)(F)F)([C:8]([O:10]C)=[O:9])[CH2:4][CH2:3]1.[OH-].[Na+]>CO>[CH3:1][N:2]1[CH2:7][CH2:6][C:5]([CH2:12][NH:13][C@@H:20]2[CH2:22][C@H:21]2[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([C:8]([OH:10])=[O:9])[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86708268HCID 86708268, compound

Product 1

HCID 68385179HCID 68385179, compoundYield 69.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 1-methyl-4-((2,2,2-trifluoro-N-((trans)-2-phenylcyclopropyl)acetamido)methyl)piperidine-4-carboxylate (160 mg, 0.402 mmol) in methanol (2 mL) was added sodium hydroxide (6M, 0.3 mL, 1.800 mmol), and the mixture was stirred at room temperature for 30 h. The mixture was purified using reverse-phase HPLC. The fractions containing the product were combined, treated with 1N HCl and concentrated. The residue was dried under vacuum to give 81 mg of product (HCl salt) as white solid. MS: (M+H)+=289.2. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.17-1.37 (m, 1H), 1.59-1.74 (m, 1H), 1.84-2.09 (m, 2H), 2.11-2.33 (m, 2H), 2.59-2.80 (m, 3H), 2.86-3.08 (m, 2H), 3.25 (d, J=7.58 Hz, 3H), 3.35-3.60 (m, 3H), 7.12-7.40 (m, 5H).

Workup

  1. customThe mixture was purified
  2. additionThe fractions containing the product
  3. additiontreated with 1N HCl
  4. concentrationconcentrated
  5. customThe residue was dried under vacuum

Sources & evidence

ORD record
ord-c4997994d56d4beca2bd256efe66b80e
Source dataset
uspto-grants-2014_10
Patent number
US08853408B2

Reaction notes

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